Ibrutinib (1-[(3R)-3[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl] piperidin-1-yl]prop-2-en-1one) has the following chemical structure (I):

This pharmaceutically active ingredient is known from WO 2008/039218. Ibrutinib is an inhibitor of bruton's tyrosine kinase (BTK). BTK is a key mediator of at least three critical B-cell pro-survival mechanisms occurring in parallel regulating B-cell apoptosis, cell adhesion and lymphocyte migration and homing. By inhibiting BTK ibrutinib drives B-cells into apoptosis and/or disrupts cell immigration and adherence to tumor-protective microenvironments. Ibrunitib is therefore suitable for treating chronic lymphocytic leukemia (CLL) and small lymphocytic lymphoma (SLL) which are B-cell non-hodgkin lymphomas (NHL). It is marketed in the US under the name Imbruvica.
Crystalline polymorphic forms of ibrutinib are disclosed in WO 2013/184572.
Pharmaceutical formulations comprising ibrutinib are disclosed in WO 2014/004707A1.
Ibrutinib has a very low solubility in water e.g. form A of ibrutinib shows according to WO 2013/184572, an observed aqueous solubility of only about 0.013 mg/ml at about pH 8. The solubility strongly depends on the pH. This results in problems in the bioavailability of the active ingredient, first because of the low solubility, and second its solubility depends on the pH value in the stomach of the patient. Particular problems arise from patients wherein the pH value is altered, e.g. due to physiological variability, diseases or premedication such as PP-inhibitors. Therefore, there is a need for oral pharmaceutical compositions that contain ibrutinib in a form which is highly soluble and thus provides a reliable bioavailability of the active ingredient.
As further forms of ibrutinib, both WO 2013/184572 and WO 2014/004707 generally disclose pharmaceutically acceptable salts of ibrutinib, including acid addition salts. However, none of these documents discloses any properties of specific salts. Further, none of these documents discloses methods how to obtain such salts, nor discloses that such salts have been obtained.
When one tries to prepare acid addition salts of ibrutinib following conventional procedures of the preparation of acid addition salts of pharmaceutical ingredients, high amounts of impurities are formed. That is, preparation of acid addition salts by a conventional method is not suitable for the preparation of pharmaceutical products comprising this active ingredient.